“Why don’t men approach women anymore?” This question, posed increasingly by women to divorce attorney James Sexton, reveals a crisis in modern dating culture. In his revealing interview on Soft White Underbelly, Sexton—after 25 years observing relationship patterns through thousands of divorce cases—explains why traditional courtship has collapsed and what’s replaced it.
The answer isn’t what most people want to hear. Dating in the 2020s has fundamentally broken down, creating a generation disconnected from romantic connection in ways previous eras never experienced.
The Question That Reveals Everything
When women ask Sexton, “Why don’t men even talk to women anymore?” his response is brutally honest:
“Are you seriously asking that question? After how many years of being told, ‘Leave women alone. Don’t talk to them. You’re being disgusting when you even say hello to them.’ Don’t talk to them at the gym. Don’t talk to them on the street. Don’t talk to them at a bar. Don’t talk to them when they’re with their friends. Definitely don’t talk to them when they’re alone.”
The contradiction is glaring. Society spent years telling men that approaching women in person was harassment. Now women wonder why men don’t approach anymore.
“Pick a lane, guys,” Sexton says. “If you want us to approach you, you’re going to get approached sometimes by people who you don’t want to be approached by.”
The Economics of Dating Have Changed
Beyond the social messaging problem, modern dating costs have skyrocketed in ways that fundamentally alter who can participate.
Sexton recalls his college days: “To take a girl out to a movie, you needed like 40 bucks maybe to take her to a reasonable dinner and a movie.”
Now? “A movie alone, 100 bucks, 150 bucks by the time you buy popcorn. How does a young person do that anymore?”
This economic barrier to traditional dating particularly impacts men expected to pay for dates. Young men without significant income find themselves priced out of the dating market before they can even participate.
The App Economy: Trading One Problem for Another
Dating apps emerged as a solution to the approach problem. If men can’t talk to women in person, they can connect digitally where women have opted in to being contacted.
But this created new problems. Women complain: “Why do men always want to talk on apps and then they only want to text?”
“You don’t get it both ways,” Sexton responds. “It’s not how it works.”
The Visual Economy of Apps
Dating apps introduced a brutal visual selection process that previous generations didn’t face. Before apps, attraction could develop through conversation, shared activities, or gradual exposure. Apps demand instant visual judgment.
This particularly disadvantages men who aren’t immediately visually appealing but would shine in person through personality, humor, or presence—qualities Sexton possesses in abundance.
“Twenty-six-year-old Jim Sexton, this wasn’t his fate,” he reflects. “I was a dorky guy. I was not successful. I was academic. I wasn’t particularly good-looking. I was awkward.”
What saved young Sexton? Women who “saw something in me” and invested early. In today’s swipe culture, he might never get that chance.
The Problem Poor Men Face
Sexton identifies a stark reality: “Poor men are just screwed right now because I don’t know a lot of women that are willing to invest anymore in a poor man.”
In the dating app economy, men can’t demonstrate future potential, work ethic, or personal growth. They can only display current status through photos and brief text.
“Buying stock in Jim Sexton when he was 26 years old, that’s a smart investment move,” he notes. “Buying stock in me now—you know how expensive the shares would be now?”
Young men on their way up face a brutal choice: wait until they’re successful enough to compete, or accept being filtered out by women who can afford to be selective.
The Female Perspective
This isn’t about blaming women for having standards. Successful women rationally seek partners who match their achievement level. The problem is systemic: when everyone can access everyone through apps, why would a successful 30-year-old woman date a 26-year-old man still building his career?
“I am 53 years old and the number of women in their 20s and 30s sliding into my DMs is ridiculous,” Sexton shares. These women “should be dating my sons, not me.”
They contact him because he has the markers of success: fame, money, status. Men without those markers—especially young men—struggle to compete.
What Men and Women Actually Want (And Won’t Admit)
Part of the dating crisis stems from dishonesty about what each gender actually seeks.
What Men Want
“I don’t think what men want has changed that much since the stone age,” Sexton observes. “We’ll go out. We’ll kill the animal. We’ll do the whole thing. Just be nice and let us rub up against you. Maybe make some food.”
Before delivery apps and modern conveniences, having a wife who could cook and maintain a household provided enormous value. Now? “How much is really involved in that gig?” Sexton asks provocatively.
His point: traditional male-female dynamics were built around practical necessities that largely no longer exist. Men’s core desires remain simple, but the practical benefits they historically received from relationships have evaporated.
What Women Want
Women’s desires, Sexton argues, center more on emotional connection and attention than purely physical attraction.
“The women who are sliding into my DMs are not sliding into my DMs because they’re like, ‘I want a medium-sized white boy with a pointy nose who’s in his mid-50s,'” he explains. “I have an emotional vocabulary. I have interesting things to say and I find the things other people have to say interesting.”
Women value conversation, emotional intelligence, and intellectual engagement in ways men often undervalue. But modern dating platforms don’t showcase these qualities effectively.
The Game Everyone’s Playing (And Pretending They’re Not)
Sexton identifies a core problem: “Everyone is playing games. Unless we all stand down and go, ‘Okay guys, let’s stop. This isn’t working.'”
The Text Response Game
Women create rules: “He was too eager. He texted back so quickly.”
Men respond strategically: “Okay, I’m not going to do that then.”
This creates an artificial dance where neither side communicates authentically, instead calculating optimal response times and crafting strategic messages.
The Interest Display Game
Women want men to pursue but not be too interested. Men want women to show attraction but not seem desperate. Both sides carefully calibrate their apparent interest level rather than honestly expressing their feelings.
“I’m going to pretend I don’t want to have sex with you and you’re going to pretend you don’t care how much money I make,” Sexton summarizes. “You’re lying. We all know you’re lying. So let’s just stop.”
How Modern Men Learn About Women (Or Don’t)
Sexton credits his own success with women to an unusual advantage: growing up with a sister six years older.
“When I was 12, I was around 18-year-old girls—tons of 18-year-old girls,” he recalls. “They’re all talking about guys and what they like and don’t like and I’m absorbing all of this.”
By college, he was “incredibly comfortable talking to women” while his male friends struggled. “It’s actually easier to talk to women than it is to talk to men in some ways because they’re super into emotional vocabulary.”
Most men don’t have this advantage. Without sisters, female friends, or mentors willing to explain what women want, men fumble through modern dating guided only by contradictory internet advice.
The Red Pill Response
When young men struggle in the dating market, some turn to online communities that teach them “how to meet women, how to attract high-value women, how to be a high-value man.”
Sexton pushes back on characterizing this as “tricks” or “games.” He compares it to women wearing makeup—enhancing your presentation to be more appealing.
“Is makeup tricking?” he asks. “I don’t think it’s lying. I think it’s accentuating the positive.”
Similarly, men learning to present themselves more attractively to women aren’t necessarily being dishonest. They’re learning the dating game rules they weren’t taught naturally.
The problem arises when advice crosses from “present your best self” to “manipulate through deception.” But Sexton argues most relationship advice for men falls in the former category.
What Happened to Just Dating?
“People were talking the other day about how Gen Z doesn’t go out on dates,” Sexton notes. “Part of that is how the hell could you afford to go out on a date now?”
But economic barriers aren’t the only issue. The entire concept of casual dating—spending time with someone to see if attraction develops—has largely disappeared.
Modern dating culture pushes people toward instant decisions about long-term compatibility. Apps ask users to evaluate life partner potential from a few photos and a bio. There’s no space for the gradual discovery that characterized traditional courtship.
The Attention Economy
Women want “your attention and your undivided attention,” according to Sexton. But modern life makes undivided attention increasingly rare.
Phones constantly interrupt. Work bleeds into personal time. Social media creates the illusion of connection while preventing real intimacy.
The couples Sexton identifies as successfully married prioritize attention-giving. They take regular trips together away from distractions. They maintain focus on each other rather than constantly checking devices.
The Performance Problem
Perhaps the deepest issue: “We’ve become very performative as a society,” Sexton observes. “Everyone’s life has become like a 1990s TV drama.”
Instagram relationships aren’t built for genuine connection but for content creation. The engagement video, the wedding planning, the honeymoon content—each milestone becomes a performance for an audience rather than an intimate experience.
This performative approach to modern romance creates relationships optimized for appearance rather than substance. Couples curate their image rather than tending their actual connection.
Solutions? Maybe Not
Sexton doesn’t offer easy solutions because he doesn’t believe easy solutions exist. The modern dating crisis stems from fundamental changes in:
- Economic structures (two-income households as necessity)
- Social norms (elimination of traditional gender roles without replacement)
- Technology (apps that commodify human connection)
- Culture (performative social media lifestyles)
- Expectations (everyone wanting Instagram-perfect relationships)
These forces aren’t easily reversed.
What Actually Works
Despite the bleak analysis, Sexton identifies factors that help people succeed in modern relationships:
Honest communication about expectations. The successful couples he knows explicitly discuss what they want rather than expecting partners to guess.
Recognizing what you actually bring. Understanding your unique value helps you find complementary partners rather than competing with them.
Focusing on in-person connection. Apps can facilitate introductions, but real attraction develops face-to-face through conversation and shared experiences.
Rejecting the performance. Building genuine intimacy requires dropping the Instagram persona and being authentically yourself.
Understanding the economics. Acknowledging that relationships involve exchange helps you find fair partnerships rather than feeling exploited or entitled.
The Brutal Reality
After 25 years observing relationship formation and dissolution, Sexton’s conclusion is sobering: “I don’t think anyone understands the rules anymore. I tell you how many divorce clients I have that call me and are like, ‘I can’t believe I’m single again. This is horrible. It was never like this when I was single before.'”
People who were last single in the pre-app era find themselves bewildered by modern dating culture. The rules changed completely, and nobody provided a guidebook.
Young people navigating this landscape for the first time face even greater challenges. Without any memory of how dating worked before, they assume the current broken system is normal.
The Uncomfortable Question
Sexton poses a question few want to consider: “What is the problem we think marriage is going to solve?”
If the answer is loneliness and validation, perhaps there are better solutions than a legal institution with a 70% failure rate accessed through a dating system that leaves most people frustrated and disconnected.
Maybe modern dating isn’t broken—maybe it’s revealing that the destination (marriage) wasn’t worth pursuing in the first place.
Or maybe, as Sexton suggests, we need to “all stand down” and stop playing games. To communicate honestly about what we want, acknowledge the economic realities of relationships, and build connections based on genuine compatibility rather than Instagram potential.
Until that happens, expect more women wondering why men won’t approach, more men feeling shut out of the dating market, and more divorce lawyers staying busy cleaning up the mess.
Credit: James Sexton interview on Soft White Underbelly YouTube channel. James Sexton is a New York divorce attorney and author of “How To Stay In Love” and “If You’re In My Office It’s Already Too Late,” available on Amazon.